5,8-Dihydroxy-1,4-naphthoquinone

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5,8-Dihydroxy-1,4-naphthoquinone
IUPAC name

5,8-dihydroxynaphthalene-1,4-dione

Other names

Dihydroxynaphthoquinone

Identifiers
PubChem 10141
ChemSpider 9735 YesY
ChEMBL CHEMBL274056 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H6O4
Molar mass 190.15 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Naphthazarin, often called 5,8-dihydroxy-1,4-naphthoquinone or 5,8-dihydroxy-1,4-naphthalenedione (IUPAC), is a naturally occurring[1][2] organic compound with formula C
10H
6O
4, formally derived from 1,4-naphthoquinone through replacement of two hydrogen atoms by hydroxyl (OH) groups. It is thus one of many dihydroxynaphthoquinone structural isomers.

Naphthazarin is soluble in 1,4-dioxane from which it crystallizes as deep red needles that melt at 228−232 °C.[3]

Synthesis

Naphtharazin can be prepared by condensation of 1,4-dimethoxybenzene with 2,3-dichloromaleic anhydride followed by reductive dechlorination and reoxidation.[4][5]

Naphtharazin can also be obtained by oxidation of 5,8-dihydroxy-1-tetralone with manganese dioxide (MnO2).[3]

References

  1. ↑ Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.
  2. ↑ Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce.
  3. ↑ 3.0 3.1 J. Khalafy and J.M. Bruce (2002), Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139.
  4. ↑ Lewis J.R. and Paul J.J.(1977). Z. Naturforsch., B, 32: 1473. Quoted by Khalafy and Bruce.
  5. ↑ Huot R. and Brassard P. (1974). Can. J. Chem., 52: 838. Quoted by Khalafy and Bruce.
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